(2S,3R,4S,5R,6R)-2-[4-[(2R,3S)-5-[(1R,2S)-1,3-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)propyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 049fae8e-5c24-4382-918d-724d16d322d1
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[4-[(2R,3S)-5-[(1R,2S)-1,3-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)propyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)C(C(CO)C5=CC(=C(C=C5)O)OC)O
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)OC)[C@@H]([C@H](CO)C5=CC(=C(C=C5)O)OC)O
• InChI: InChI=1S/C33H40O14/c1-42-23-9-15(4-6-21(23)37)19(12-34)27(38)17-8-18-20(13-35)31(47-32(18)25(11-17)44-3)16-5-7-22(24(10-16)43-2)45-33-30(41)29(40)28(39)26(14-36)46-33/h4-11,19-20,26-31,33-41H,12-14H2,1-3H3/t19-,20-,26-,27+,28+,29+,30-,31+,33-/m1/s1
• InChI Key: INHOOZJIXKSZFG-KZACDRMVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₄
• Molecular Weight: 660.70 g/mol
• Exact Mass: 660.24180595 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5194	51.94%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6207	62.07%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8246	82.46%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8590	85.90%
P-glycoprotein inhibitior	+	0.5925	59.25%
P-glycoprotein substrate	-	0.5405	54.05%
CYP3A4 substrate	+	0.6411	64.11%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.7781	77.81%
CYP3A4 inhibition	-	0.9172	91.72%
CYP2C9 inhibition	-	0.8204	82.04%
CYP2C19 inhibition	-	0.7878	78.78%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.8954	89.54%
CYP2C8 inhibition	+	0.6792	67.92%
CYP inhibitory promiscuity	+	0.5396	53.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5547	55.47%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9179	91.79%
Skin irritation	-	0.8468	84.68%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7113	71.13%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9015	90.15%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8069	80.69%
Acute Oral Toxicity (c)	III	0.7301	73.01%
Estrogen receptor binding	+	0.7936	79.36%
Androgen receptor binding	+	0.6211	62.11%
Thyroid receptor binding	+	0.5941	59.41%
Glucocorticoid receptor binding	+	0.6807	68.07%
Aromatase binding	+	0.5530	55.30%
PPAR gamma	+	0.6718	67.18%
Honey bee toxicity	-	0.7482	74.82%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7150	71.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.08%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.39%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.77%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.81%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.03%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.89%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.69%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.13%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.15%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.95%	86.33%
CHEMBL2535	P11166	Glucose transporter	85.57%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.54%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	85.43%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.18%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.81%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	84.70%	90.20%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.70%	99.15%
CHEMBL4208	P20618	Proteasome component C5	84.43%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.94%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.48%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.02%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.80%	92.62%

Plants that contains it

• Iodes cirrhosa

Cross-Links

• PubChem: 162898992
• LOTUS: LTS0032209
• wikiData: Q105116207